Zero to Assassin
by assassinwriter
Summary: Instead of killing the Monstrous Nightmare Hiccup left and went exploring for a bit before he decided to go to Rome. When he is in Rome he runs into a Brotherhood of Assassins. HiccupxOC since there are enough HiccupxAstrid stories out there and at least check it out before you decided not to read it please. rated M for language, blood, and maybe just maybe sexual content later.
1. Chapter 1

**A/N: The assassin in question are the assassins from Assassin's Creed, so you can just imagine the assassin in those types of robes. Anyways enjoy. **

Chapter 1

Hiccup walked into the cove where he kept Toothless and said "We're leaving buddy, come on. We're going on a vacation forever."

Toothless bounced over and tackled Hiccup before licking him repeatedly. "Stop, stop" Hiccup said pushing Toothless away from him. "You know that doesn't come out" Hiccup said after stopping Toothless.

Hiccup packed his things on Toothless then took off into the sky. However they were unaware that a certain blond had seen them take off and was certainly on her way back to the village.

When Astrid got to Stoick's house she pounded on the door a few times.

"I'm coming" She heard someone say from behind the door.

A few seconds later Stoick opened the door and said "Oh, Astrid what can I do for you?"

"Hiccup flew off on a dragon" Astrid said quickly, but still slow enough to be understood.

Stoick stood there for a few seconds making sure he heard what Astrid said and replied with "Hiccup flew off on a dragon?"

"Yes he flew off on the back of a black dragon and I can show you where" Astrid said adding in more detail.

Stoick placed a hand on Astrid's shoulder and asked "Are you sure your jealously isn't getting the better of you?"

That made Astrid furious and she smacked Stoick's hand away and said "My jealously is not getting the better of me and when Hiccup doesn't show up tomorrow you'll see I'm right." Astrid then turned around and stormed off.

Hiccup and Toothless were a good distance away by this time. "So, bud what you want to do now" Hiccup asked and got a coo in response.

"Go exploring it is than" Hiccup said.

The next day at the dragon killing arena everyone was waiting for Hiccup to show up, but he never did show up. "Do you believe me now" Astrid asked Stoick.

"Maybe he just lost track of time" Stoick said not wanting to believe what Astrid said.

"He's two hours late Stoick, that isn't a 'sorry I lost track of time' lateness" Astrid said.

Stoick sighed and said "Fine, show the place Hiccup supposedly flew off on the back of the dragon."

After a short walk to the cove were Hiccup and Toothless left from. When they got there Astrid showed Stoick the burned spot where Toothless slept and multiple black scales throughout the cove. Stoick studied the area for a will then asked "Are you sure that you saw them?"

"Positive" Astrid replied simply.

Stoick then clenched his fist in rage as knowing that is son had betrayed him, the village, and the whole Viking way. "Looks like I have an announcement to make" Stoick said before walking back to the village.

When Stoick arrived at the killing ring, with Astrid close behind, someone asked where Hiccup was. Stoick scowled and said "Hiccup left Berk after committing a treasonous act and is henceforth considered a traitor and an outcast, also he is no longer my son."

Everyone gasped at the news that Hiccup would commit treason. "What did he do" Someone asked.

"He sided with the dragons" Stoick said, then continued with "Now I believe we have a Monstrous Nightmare to kill, and since Hiccup is now banished and a traitor the honor of killing it will got to Astrid Hofferson."

Astrid's eyes light up with joy at the news, no one else dared speak figuring that Stoick just wanted to move on from his disappointment of a son. Astrid walked over and grabbed her axe then entered the killing ring.

The Monstrous Nightmare was released from his cage, well more like burst out of his cage, and ran around for a few seconds before its eyes fell on Astrid. The Monstrous Nightmare fired some of its lava like breathe at Astrid, who quickly dodged it. She then charged the Monstrous Nightmare and tried to bring her axe down on its head, but the Monstrous Nightmare quickly got out of the way. The Monstrous Nightmare capitalized on its action with a swipe of its tail. Astrid jumped over the tail and charged the Monstrous Nightmare. The Monstrous Nightmare moved, but Astrid managed to cut its side a bit. The Monstrous Nightmare screeched and pain and fire some more of its lava like breathe at Astrid. Astrid barely managed to escape the fire breathe. She then charged the Monstrous Nightmare again and managed to strike it in the head, but it was only a glancing blow, leaving a cut on the Monstrous Nightmare's head. The Monstrous Nightmare roar in pain and rage again and charged Astrid. Astrid rolled out of the way of the Monstrous Nightmare. In its rage the Monstrous Nightmare slammed into the wall of the killing ring and stunned itself. Astrid took the opportunity to charge the Monstrous Nightmare. Astrid then swung her axe down on the Monstrous Nightmare's neck effectively decapitating it.

The crowd erupted in a cheer and was chanting Astrid's name. Astrid was smiling brightly over the fact that she killed her first dragon and had become a true Viking.

At this time Hiccup and Toothless were a good distance away from Berk heading east to explore the archipelago.

Six months passed since Hiccup left Berk and they celebrated Hiccup leaving since they considered Hiccup was a curse. However Stoick stayed in his house, barely leaving, for the first month, then throw himself into his work. Gobber was depressed that Hiccup left, he loved like the son he never had and gave him all the love he could, which apparently wasn't enough. Astrid was happy with the praise she got since she killed a few more dragons during the raids. Snotlout got even more arrogant, if that was possible, over the fact that he was next in line to be chief and asked Astrid out even more. Fishlegs was sad, but not depressed like Gobber, he like Hiccup and wished that he actual stuck up for him instead of shunning him out of fear of getting beat up. The twins were the exact same, but did miss Hiccup a little bit, since he was always destroying things.

Hiccup had spent the six month exploring the archipelago and decided to head to Rome.

Hiccup and Toothless landed in the woods outside of a town along the coastline. "Stay here bud I'm going to go get some supplies" Hiccup said dismounting Toothless, who wobbled in worry. "Don't worry bud I'll be fine" Hiccup said patting Toothless on the head then walked off to the town.

After a 15 minute of walking Hiccup arrived at the town and started to walk around to find the market place. While he was walking around he saw a group of Roman soldiers engaged in a fight with two hooded figures. During part of the fight the hood of one of the figures came down showing a girl with long crimson red hair and emerald green eyes. The red haired girl didn't notice a Roman soldier was coming up behind her. Hiccup rushed to get to the girl. The girl noticed the Roman soldier when he was right behind her, but she was too late to react as the soldier's axe was already coming down. The girl was suddenly shoved to the side and out of the way of the axe by Hiccup.

Then it all went black.

**A/N: Hope you enjoyed the chapter please Favorite, Follow, and Review. Also I should be updating this every Tuesday.**


	2. Chapter 2

**A/N: Hey Merry Christmas. Well that's all I have to say at this point so enjoy the story.**

Chapter 2

Hiccup was lying in a small bed with Toothless at the foot and two hooded figures on the sides. He groaned and moved his hands to his head, which felt like a Thunderdrum was roaring inside, where he felt gauze and a bandage. He slowly opened his eyes and took a look around. "Where am I" Hiccup groaned.

"You're in the infirmary at our hideout" One of the hooded figures said removing their hood revealing a man in his mid-50's with short dark brown hair and some gray mixed in, blue eyes, and small beard around the mouth also with some gray hairs.

Just Toothless jumped on the bed and started to lick Hiccup. "Uh, stop it Toothless" Hiccup said trying to push Toothless off of himself.

Toothless eventually got off of Hiccup and the other hooded removed their hood showing the same red headed girl from before and now that Hiccup got a better look at her she looked only a year or two older than himself. "How do you feel" the girl asked.

"Fine other than the mother of all headaches" Hiccup replied which caused the girl and man to chuckle.

"What's your name kid" the man asked.

Hiccup opened his mouth to say speak, but he couldn't remember his own name. He thought for a minute trying to remember it, but couldn't and said "I'm sorry I don't remember."

"What do you mean you don't remember" the girl asked.

"I can't remember my name for some reason" Hiccup replied.

"Maybe that blow to the head gave him amnesia" the man said to the girl.

"Ok what do you remember" the girl asked.

"Flying on Toothless to a city. Landing in the woods near the city. Went to get supplies in the city. Where I saw two hooded figures, much like yourselves, fighting some Roman soldiers. Then push a pretty red headed girl out of the way of a Roman soldier with an axe. Then nothing" Hiccup replied. The girl had blushed when Hiccup unknowingly called her pretty.

"What about before that" the man asked.

"Nothing other than the fact that Toothless is my best bud. I'm sorry, but that is all I can remember about my life" Hiccup replied.

"That's ok kid, must people don't survive an axe to the head" the man said putting a comforting hand on Hiccup's shoulder.

"Mind telling me what happened after I blacked out" Hiccup said.

"Sure" The girl said and started to explain what happened next.

FLASHBACK

The girl and the other hooded figure hand finished getting rid of the Roman soldiers and the girl ran over to Hiccup to check if he was still alive. Much to the girl's relief he still was, but was bleeding badly from his head wound. The girl quickly took out some gauze and bandages and started to put them on Hiccup's wound to try and stop the bleeding, or at least slow it down.

"Linda what are you doing we need to go" the hooded figure asked in Latin (**A/N: Latin was the spoken language in the Western Roman Empire while Greek was spoken in the East**).

"I'm not leaving him here" Linda replied back and picked Hiccup up.

The hooded figure removed his hood in frustration reviling a man in the mid-20's, with short light brown hair, and hazel eyes. "Fine give him here it'll be easier if I carry him" the man said holding out his arms knowing it's pointless argue with Linda in this type of situation.

"Thank you Alex" Linda said putting Hiccup in the man's arms.

"Whatever let's just get out here before more show up" Alex replied and ran off towards the woods with Linda on his heels.

They were running through the woods when all of sudden Toothless jump out in front of them and snarled. That cause Alex and Linda to stop dead in their tracks. They stayed frozen as Toothless gave them the death glare. Alex and Linda has had zero experience with dragons since there were basically none in Rome. Toothless approached Alex and Linda slowly.

"I'm going to give the kid to you and run for the hideout while I keep him distracted" Alex whispered to Linda.

"No I'm not going to leave you here alone" Linda replied.

"I'll be fine I can hold my own" Alex replied and slowly gave the unconscious Hiccup to Linda.

When Alex made the transfer Toothless eyes quickly locked onto Linda and snarled even louder. Linda froze for a second before she noticed that Toothless had a saddle on him.

"Hey Alex I think this kid is that dragon's rider" Linda whispered.

"What that crazy there's never been a tale of anyone riding a dragon" Alex replied back.

"Then how do you explain the saddle" Linda shot back.

Alex looked at Toothless and did in deed see a saddle. "Ok so maybe he his, but that doesn't help out since he his unconscious" Alex said.

"Took him back I have an idea" Linda said and handed Hiccup back to Alex.

Toothless got closer and snarled at Alex. Linda got between them, but was off to the side a little so Toothless could see Hiccup. Linda drew her sword and Toothless got into a defensive position and snarled some more. Linda tossed the sword away and held up both her hands and removed the hidden blades and tossed them away as well. Linda then put her hands out in front of her in a calming gesture and said "Hey there big guy. I'm guessing the person my friend is holding is your rider."

She saw Toothless relax a bit and continued "Look we didn't hurt him some Roman soldiers did that part. In fact your rider saved my life, but got injured and will most likely die if we don't help him."

Toothless relaxed almost completely and got a concern look and cooed in concern as well. "Yeah so we need to get back to our hideout so we can treat him way don't you come with us" Linda said and reach a hand out in a friendly manner. Toothless leaned in and rested his snout in the palm of Linda's hand. That caused Linda to smile and she scratched Toothless a bit before picking up her swords and hidden blades.

"Let's go" Linda said and started to run off towards their hideout followed by Toothless then Alex.

END OF FALSHBACK

"That's what happened" Linda said "and you should have seen the look on everyone face when we brought your dragon with us it was hilarious."

Everyone then heard a knocking sound and looked to see Alex leaning on the door frame. "So how is our dragon rider doing" Alex asked in Latin since he didn't speak Norse like Linda or the older man.

"Other than a killer headache and some amnesia he seems fine" Linda replied back in Latin.

"Ok just thought I would drop by" Alex said before leaving.

"Ok bye" Linda said then turned back to Hiccup.

"Don't worry about him he's all ways in a grumpy mood" Linda said Norse.

"Ok, by the way what's you name" Hiccup asked.

"Linda and that is the Grand Master the head of our organization" Linda said while pointing her thumb at the older man.

"Thanks for helping" Hiccup said.

"Not problem at all and thank you for saving Linda" the Grand Master replied.

"Now since you can't remember your name we'll have to give you one, how about Ryder" Linda said.

Hiccup thought about it and said "What do you think bud" looking at Toothless. Toothless nodded his head in approval and Hiccup said "Ryder it is than" with a smile.

**A/N: Hey hope you enjoyed the chapter and next one should be posted next Tuesday. I hope you have a Merry Christmas and as always Favorite, Follow, and Review.**


	3. Chapter 3

**A/N: Hey sorry for the late update. Thanks for the Favorites, Follow, and Reviews. Anyways I started calling Hiccup by Ryder since that is the name they knew him by, but it that is to confusing then I can change it. Also if you see so text in a foreign language and then () next to it. Whatever is inside the() is what language it is and just use google translate for the translation, but I usually make it pretty easy to tell what it is. Anyways enjoy the chapter and Hiccup = Ryder**

Chapter 3

The next couple of days Ryder spent in bed with different people visiting him and wanting to see Toothless. Several of them brought fish for Toothless and they found out that Toothless like mackerel the most and hated eels. Linda basically stayed with Ryder the entire time only leaving to sleep, shower, or use the bathroom. Linda told Ryder about Rome and its culture along with teaching him Latin and Greek; she also taught him what little she knew about Viking culture she knew. They quickly determined that Ryder befriending Toothless was the reason he left.

During those days Ryder and Toothless had two more frequent guest. One was named Mark and the other was named John. Mark was around 6 feet tall, 17 years old, same age as Linda. He had short brown hair, hazel eyes, and wear blue robes. John was around 6' 3", also 17 years old. He had dirty blonde hair that went to his collar, blue eyes, and wear white robes.

Ryder was lying in his bed in the infirmary, with gauze and a bandage still on his head, and Toothless was at the foot, when there was a knock on his door. "Who is it" Ryder asked.

"Linda" was the reply.

Ryder got up and walked over to the door, stepping over Toothless's tail that was on the floor, and opened it. There Linda was in maroon colored robes and said "Hey Ryder how are you feeling? Any memories come back?"

"Fine thank you and no none of my memories have come back" Ryder said.

"Well I'm glad you are feeling better, and as for the memory thing. Don't worry about it ok? It'll come back when it comes back" Linda said putting a hand on his shoulder at the end. "Now, if you're feeling up to it would you like to grab some lunch with me?"

"Sure sound nice. It'll be good to get out of this room" Ryder replied.

"After that maybe I could show you around the compound" Linda asked.

"Sounds like a good use of the afternoon" Ryder said.

"Ok let's go" Linda said extending her hand for him to take. Ryder hesitantly takes Linda's hand. Linda noticed this hesitation and asked "Are you ok Ryder you seem a little nervous?"

"I-I'm…f-fine" Ryder stuttered a looked away trying to hind.

Linda looked at Ryder for a second trying to figure out what was making Ryder so nervous. _"Why is he so nervous he's meet just about everyone on the compound over the last few days and seemed to like everyone and be liked by everyone"_ Linda thought to herself. Then she looked down at he's hand that was in hers and then it clicked. _"Looks like someone isn't use to being around girls or women that much."_ Linda thought to herself and cracked a smile. _"But I must admit he is kind of cute when he's nervous."_

"Come Ryder I won't bite I promise" Linda said, but she couldn't resist leaning in and saying "unless you're into that sort of thing."

Ryder went redder than Linda's robes and Linda that he was about to overheat. Ryder immediately back away from Linda and said "No…no…no…I'm…n-not" but never finished before tripping on Toothless's tail and landing flat on his back. That caused Linda to burst out laughing along with Toothless.

"It's not funny" Ryder protested pitifully.

"You're right Ryder it wasn't funny. It was hilarious" Linda said before going into another fit of laughter. "Come on let's get you to the mess hall for some food" Linda said after her laughing fit and stuck her hand out for Ryder to grab.

Ryder grabbed Linda's hand and she pulled him up off the floor. Ryder muttered a quick thank you and they head off to the mess hall with Toothless following close behind.

MESS HALL

Linda, Ryder, and Toothless arrived at the mess hall got there food which consist of some chicken, a small salad, a fruit, bread, and water; while Toothless got a bucket of fish. They were looking for a place to sit when they heard someone call their names. They looked in the direction of the noise and saw that it was Mark, who was sitting next to John, and he was waving them over. Linda and Ryder looked at each other before making their way over the Mark and John.

"Quomodo futurum sit" (Latin) Mark asked.

Ryder looked up and put a hand on his chin trying to remember what that meant. "Ah, fine thank you. How is it going with you" Ryder answered in Norse.

"Fine thanks and it seems like you're learning Latin pretty well" Mark said also in Norse.

"Thanks, but the credit goes to Linda for being such a good teacher" Ryder replied.

"Hey you're a good student" Linda said.

"Anyways got any memory back yet" John asked.

"No not yet" Ryder replied sheepishly while rubbing the back of his neck.

"Give it time. Good things come to those who wait" John said.

"Thanks" Ryder replied with a small smile.

"So what do you two have planned for the rest of the day? Another language learning lesson back in the infirmary?" Mark asked.

"No, I was going to show Ryder around the compound" Linda replied.

"Sounds fun mind if we join you" Mark asked.

"Yeah that sounds fine by me. What about you Ryder" Linda replied.

"Yeah that's fine" Ryder said before taking a bite out of his bread.

The rest of the lunch was spent with some small talk, jokes and funny stories, and some useful information about the nearby towns. They got up and hand their dishes to the kitchen staff and walked out of the mess hall

In a hallway just outside side of the mess hall they were deciding where to go first. They just decided to follow the hallway they were in and go from there. While walking through the hallway they came across the Grand Master. "Hello children" the Grand Master said.

"Hello Grand Master" they all replied in sync.

"How are you feeling today Ryder" the Grand Master asked.

"Fine thank you" Ryder replied.

"That's good to hear, and I do hope your memory returns it, must be difficult not knowing about your past" the Grand Master said.

"It's a little annoying not remembering anything about my past, but I'm doing fine regardless" Ryder replied.

"Well it's good to see you in such high spirits" the Grand Master said.

"I've been meaning to ask what exactly your organization is" Ryder said.

"It can be a bit difficult to explain without coming off as bad, so why don't you come by my room after your tour of the compound and I'll tell you about it" the Grand Master said.

"That's ok I'm sure Linda, Mark, or John could explain it to me to just fine. I wouldn't want to take up any of your time" Ryder replied.

"It won't be a problem at all, in fact one of my duties as Grand Master is to inspect new recruits" the Grand Master said.

"Ok then I'll stop by your room later today" Ryder said.

"I'll see you all later" the Grand Master said and started to walk off.

"Wait, how did you know about our tour with Ryder" Mark asked.

"I have my resources" the Grand Master said looking back with a small smile.

**A/N: Hope you enjoyed the chapter and as always please Favorite, Follow, and Review.**


	4. Chapter 4

**A/N: Hey sorry for the late update my sleep schedule was messed up so right after I got home from school I went to bed and didn't get started on this chapter till 10:47 p.m. Anyways hope you enjoy the chapter. Oh and remember Ryder = Hiccup.**

Chapter 4

Ryder, Linda, Mark, and John were currently following the hallway, were they had a chat with the Grand Master, continuing the tour of the compound. When they reach the end of the hallway they came into a room with people sparing with each other and a few people climbing makeshift building walls.

"This is the training room" Linda said, "Here you can practice your combat skills along with your climbing."

"Yeah and I'm the best there is" Mark said playfully with his nose held high.

"By best there is you mean best at getting his ass kicked by me" Linda said.

John leaned to a confused Ryder and whispered "Linda is the best in our age group."

"John we are the people within 3 years of each other" Mark pointed out.

"True most people don't really join till they are about 23 years old anyways" Linda said after thinking if she knew anyone in the area around their age.

"Anyways ready to move onto the next spot on our tour" Mark said.

"Yeah" Ryder simply said.

They exited the training room and went to the barracks. The barracks were a set of two story buildings each with 10 rooms in each one with two bathrooms on the bottom floor.

"These are the barracks" Mark said, "This is where we live and where you will be staying if you decide to stay here with us."

"Does everyone on in your organization live here" Ryder asked.

"No some people live in cities and have places there along with family" Linda said. "Also our organization is massive. It spans the entire Roman Empire and keeps going into Asia and Africa."

"Asia and Africa?" Ryder asked confused.

"I'll show you a map later" Linda said putting a hand on Ryder shoulder.

"So the Grand Master is in control of the entire thing" Ryder said shocked.

They looked at Ryder confused at why he would think that, then Linda remembered that she told Ryder that the Grand Master was the head of the organization. "Ryder when I said the Grand Master was the head of the organization, I meant this branch of the organization. There are multiple branches to cover everything" Linda said.

"Yeah there is another branch and Grand Master for the East of side of the Roman empire and one across the Mediterranean Sea there is one as well" Mark said.

"We don't really know where any of the others are" Linda added in.

"Anyways enough of this boring educational stuff, let's hit the next spot on the tour" Mark said grabbing Ryder and Linda by the arm and dragging them off with John close behind.

Mark dragged them to the armory and forge. When they arrived at the forge Ryder had a sudden wave of memories working in the forge with Gobber, but was unable to give Gobber a face or body much less a name. Ryder staggered a bit from the rush of memories, but Linda caught him. "You ok Ryder" Linda said voice full of concern.

"Yeah just remembered some things about my past" Ryder said.

"Really what" Linda asked.

"I was in a forge working most likely I was an apprentice" Ryder said.

"Do you know who you were an apprentice to" Mark asked.

"Sorry, I can really just remember the stuff I learned, but nothing else" Ryder said rubbing the back of his neck.

"No need to be sorry. Most people wouldn't have leaved from an axe to the head" John said.

"True you must be one lucky SOB" Mark said putting a hand on Ryder's shoulder comfortingly.

"Maybe visiting the forge might help you get some more of your memory back" Linda said and walked into the forge. Ryder, Mark, and John followed.

When they entered the forge they saw several people working on weapons. One man looked at them and waved the over. He had short dark brown hair, brown eyes, and a thick brown bread the covered his mouth and cheeks. He looked to be in his mid-30's and was wearing a tattered green short sleeve shirt with brown pants and an apron.

"Well if it isn't Linda, Mark, John, and Dragon boy" the man said in Norse.

"Hey Albus how's it going" Linda said.

"Fine, what brings you four down to the forge" Albus asked.

"Just showing Ryder around the compound" Linda said.

"Oh, so you've decided to join our little Brotherhood after all" Albus said.

"No not yet the Grand Master is going to talk to me be about it later" Ryder said.

Albus nodded in confirmation. "Anyways is it ok Ryder helps around the forge for a bit" Linda asked.

"Why" Albus asked confused.

"When we entered the forge Ryder gained some of his memory back. The memory he got back was him working in the forge, so I was wondering if it was ok for him to help out and see if we can get more of his memory back" Linda said.

Albus thought about for a minute trying to figure out if there was anything that he could do without having to worry for Ryder's safety. "I got a few swords that need to be sharpened think you could do that" Albus said.

"Yeah that should be easy enough" Ryder said.

"Then get to it" Albus said handing him some the swords which where lighter than the Viking weapons.

The next hour was spent with Ryder sharpening swords and chatting with Linda, Mark, John, and Albus.

After Ryder got done with sharpening the swords Albus inspected them. "Well I must say I'm quite impressed with how well these are sharpened" Albus said.

"Really" Ryder asked feeling proud.

"Yes these are sharpened with the skill of a seasoned blacksmith" Albus said.

"Looks like someone is one good in the forge" Linda said putting her arm around the Ryder's shoulder.

"Thanks" Ryder said with a nervous chuckle.

"Anyways I think we should get you to the Grand Master before it gets too late" John said.

Ryder sighed and said "I guess I should go talk to the Grand Master. By the way is it wrong to be really scared of him?"

"No not the slightest" Linda said grabbing Ryder's arm and dragging him to the Grand Master's room.

**A/N: Hope you enjoyed the chapter and please Favorite, Follow, and Review.**


End file.
